Lithium Chloride → (S)-3-(4-(5-fluoro-2-(pyrimidin-2-yl)pyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

HRID 525411ノート

反応式

HRID 525411 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)[C:5]([F:28])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC.[Cl-].[Li+]>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[F:28][C:5]1[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)=[CH:7][C:2]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[N:3][CH:4]=1

参加物

7

反応物 3

HCID 433294Lithium ChlorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 89813900(S)-3-(4-(2-bromo-5-fluoropyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

生成物 1

HCID 89813820(S)-3-(4-(5-fluoro-2-(pyrimidin-2-yl)pyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one収率 20%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A microwave vial was charged with (S)-3-(4-(2-bromo-5-fluoropyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.060 g, 0.136 mmol), 2-(tributylstannyl)pyrimidine (commercially available from Frontier Scientific, Inc., Logan Utah) (0.067 mL, 0.204 mmol), lithium chloride (0.012 g, 0.272 mmol), copper (I) iodide (2.59 mg, 0.014 mmol), and DMF (2.0 mL). Tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) was added, the system was purged with argon, and the tube was sealed. The resulting mixture was stirred at 120° C. in a microwave for 1 hour. The reaction mixture was then concentrated to afford an orange oil which was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% MeOH-EtOAc) to afford (S)-3-(4-(5-fluoro-2-(pyrimidin-2-yl)pyridin-4-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.012 g, 0.027 mmol, 20% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.66 (s, 3H), 5.53 (s, 1H), 7.10-7.54 (m, 6H), 7.56-7.89 (m, 5H), 8.10-9.41 (m, 3H). m/z (ESI) 441 (M+H)+.

後処理

  1. customthe system was purged with argon
  2. customthe tube was sealed
  3. concentrationThe reaction mixture was then concentrated
  4. customto afford an orange oil which
  5. customwas purified

出典と根拠

ORDレコード
ord-00f4f4b4de5a4a84b022863a9faff122
出典データセット
uspto-grants-2016_05
特許番号
US09340549B2

反応ノート

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